Phenol → 2-Chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrile

HRID 81023노트

반응식

HRID 81023 반응식
[Cl:1][C:2]1[N:9]=[C:8](Cl)[CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5].[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:9]=[C:8]([O:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[C:6]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[C:3]=1[C:4]#[N:5]

참가 물질

6

반응물 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 866656822,6-Dichloro-4-(4-phenoxyphenyl)nicotinonitrile

생성물 1

HCID 866656842-Chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrile수율 101%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2,6-dichloro-4-(4-phenoxyphenyl)nicotinonitrile (51 mg, 0.149 mmol, from Step 2 of Example 8), phenol (15.47 mg, 0.164 mmol) and cesium carbonate (97 mg, 0.299 mmol) in DMSO (1.5 mL) was stirred at room temperature for 15 h. The mixture was diluted with ethyl acetate (60 mL), washed with water (2×5 mL), brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0% to 20% ethyl acetate in hexanes, gave 2-chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrile as a white solid (60 mg, 75% yield). 1H NMR (500 MHz, CDCl3) δ ppm 7.52-7.73 (2H, m), 7.37-7.52 (4H, m), 7.25-7.36 (1H, m), 7.20-7.24 (1H, m), 7.08-7.18 (4H, m), 6.87 (1H, s); MS (ES+) m/z: 399 (M+H); LC retention time: 4.283 min (analytical HPLC Method A).

후처리

  1. washwashed with water (2×5 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washSilica gel chromatography, eluting with 0% to 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-e14ae2925781465bbf3b100ee2e37a9e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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